Love Me Dead
by gocrashthecar
Summary: Chuck Bass & Dan Humphrey. A match made in...jail.
1. Prologue

"Am I really doing this? Am I actually going to ask Chuck Bass to show me what his life is like? Ugh, this is probably the stupidest thing that I have ever decided to do. But, if it'll get me out of my comfort zone, I guess I'll just have to suck it up," Dan groaned to his father Rufus on the phone.

"Chuck Bass, Bart Bass's son?"

"Yep, the one and only spawn of Satan. "

"Ha, you need to get over yourself. Its only one night, how much harm could he cause in one night?"

"Do you know who you are talking about? This is the guy who happened to have sex with Blair Waldorf who happened to be dating his best friend at the time. Oh and we can't forget when he tried to violate Jenny at that one party. The guy is evil, he's maniacal, and I'm pretty sure that I won't even last 15 seconds with him."

"I doubt a 17-year-old boy can cause that much damage to a high school."

"You haven't met the guy."

"Well, just give him a shot. Listen, I've got to go pick up Jenny at her internship, it's about that time she come home for some dinner."

"Alright, I'm off to my suicide mission, wish me luck."

"Dan, you'll be fine. Stop overreacting and just go talk to him. You never know, he might be a good guy. Talk to you later."

"Bye Dad," Dan hangs up the phone groaning as he looks up at the building the Van der Bass's live in. If it wasn't for dating Serena, he wouldn't have known where they live. He sulked to the front lobby and got into the nearest elevator, pressing the button for the 22nd floor.

_Oh boy,_ Dan thought to himself. _Here I go into the lions den. _

The elevator dinged and the doors opened, and Dan Humphrey walked into the luxurious home of the Van der Bass family, coming face to face with the one and only Chuck Bass.


	2. Chapter 1

"Well, well, well as I live in breathe, Humphrey Dumpty," Chuck Bass scoffed as he stood in front of Dan. "What on Earth are you doing here? You know Serena doesn't condone of even give stalkers the time of day."

"Uh, I'm actually not here to see Serena. I'm here to see you."

"Me? Now why would you be doing that?"

"Well, I know you don't care about me or my life for that matter…."

"I don't think of you at all," Chuck interrupts Dan.

"Right, I knew that. But I've been thinking about me and my future. I have a feeling its going to be pretty grim if I keep up the image that I have right now."

"You mean, the "I'm so good I can't do anything wrong" image?"

"Yeah, that's the one. So I think it's about time for me to expand my horizons and come out of my shell."

"You're not gay, are you?" Chuck asked out loud.

"Heh," Dan laughed. "Now that's just way out of my comfort level. No, I'm not gay. I just want to live a day in the life of Chuck Bass. I want to see what an evening out on the Upper East Side will be like."

"Well I'm sure my sister gave you enough of that when you two were dating."

"Actually, we never went anyone near Manhattan when we went out. She normally came to Brooklyn and hung out with me and my family."

"Aww, how sweet," Chuck said. "Thanks for that tale of the day and the life of Serena and Dan, the mundane years."

"So you'll show me a night in the life?" Dan asked with a hopeful look on his face.

Chuck stared directly into his eyes, trying to see what Dan was thinking.

_Was he really coming over here to see the life of Chuck Bass? Does he really want to walk on the wild side? Impossible. There has to be a trick to this whole thing. Oh well, _Chuck thought. _I guess I could give him a try. It'll be interesting, that's for sure. _

"You are so lucky I'm bored," Chuck said with a hint of evil. "Get into the elevator before I change my mind. You're in for one hell of a night Humphrey."

Dan smiled and tried not to skip the ten feet to the elevator. _I can't believe it, _Dan thought. _He's actually going to take me out. I didn't expect this to happen at all. I wonder what it's going to be like. I wonder if I'm dressed well enough. I wonder if I'm thinking way too much into this. Oh hell Humphrey, stop thinking about it. It's going to be fine. _

Chuck walked into the elevator after Dan with the smuggest smile you could ever imagine on his face. Dan Humphrey had no idea what he was getting into.

**Spotted: Chuck Bass and Lonely Boy bonding? We'll see about that. **


	3. Chapter 2

Dan's cell phone chirped. He looked down at it, noticing that it was 10:00. Chuck had taken him to a bar somewhere in Manhattan, or at least that's what he thought. He was up at the bar schmoozing up the bartender and getting them some drinks. After all, they were still underage. He ended up getting some shots and walked back to the table with a tray in his hand.

"So, this is what you do on a normal night? Sit around a bar and drink your woes away?"

"I don't have any woes. Just shut up Humphrey and drink up," Chuck snapped back as he grabbed a shot in his hand.

"Um, I would but what the hell is this?"

"It's scotch straight up. What? You've never had alcohol before? That doesn't surprise me."

"Yeah, um, there's no way I'm drinking this…"

"Look, you said you wanted to live the life of me, and this is living the life of me. Now drink up before I leave you here by yourself."

Dan took one shot in his hand. "Well I guess I can have one."

"Oh no, you're not just having one. I bought 20 shots, and we're going to do 20 shots. And that's just the starter."

"W-w-what do you mean, just the starter?"

"Well," Chuck laughed. "After these shots I've got a little herbal refreshment for us." He opened his hand and inside was a tiny joint enough for two.

"Uhh," Dan hesitated. He wasn't sure if this was what we meant by living the life of Chuck Bass. This wasn't him at all, and he's not the kind of guy to get drunk. "Okay I guess its time for bottoms up."

Dan grabbed a shot and clinked his glass with Chuck's.

"Cheers," Dan said as he slammed the shot down. It was cool at first when it hit his lips, and then burned sailing down his throat.

"Yeah, cheers."

Chuck watched Dan as he threw his head back and took another shot. He couldn't help but laugh at him. It was amusing to see Dan actually thinking that the two of them were friends, because they never would be. And Dan had no idea what he was getting himself into. Chuck just didn't want to ruin his night and get him completely drunk, he wanted more. Dan was his little experiment. He'd never expect what was going to happen towards the end of the night. In fact, I don't think anyone would.

_This is going to be better than I ever expected it to be, _Chuck thought as he grabbed another shot and chugged it down. _And I can't wait._


End file.
